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The Art of Strategic
Conversation
Most people love a good chat, yet in the world of business,
conversation is often
dismissed
as wasteful – certainly
not "real" work. Office
spaces are divided into
separate rooms or
cubicles to enable people to
focus on the tasks at
hand, and not get diverted into "idle" conversations. Though managers spend much of
their time in meetings, seminars and workshops, they often lament that these activities are
boring and unproductive – mere "talkfests".
The Ancient Greeks would have been surprised by our attitude to conversation, as it was a
central part of their intellectual process. Socrates is famous for his "dialogues", and rhetoric
was one of the foundational skills sets for thinkers and leaders throughout the ancient
world.
Two types of real-world problem
To appreciate why the Greeks valued conversation so much, you need to understand an
important distinction that Aristotle made between two types of real-world problem. On the
one hand, there are problems relating to things that "cannot be other than they are". This
involves any situation where there are fixed circumstances or quantities which can be
measured and analysed – the sort of problems that are typically addressed by maths and
science. In business terms, you could think in terms of financial reporting, productivity
measures or sales figures – which all involve looking back at past performance.
However, there is a second category of real-world problem, relating to things that "can be
other than they are". These are the problems that relate to future possibilities, to
circumstances which could be different than they are. Mathematical and scientific solutions

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are of limited use in this context, because you are not dealing with fixed entities that can be
measured, but with options and opportunities that don’t yet exist.
The goal in this second sort of problem solving is not to find the "right" answer, but to create
a compelling argument about which option is best out of a range of possibilities. The great
insight that the Greeks had – and which we have forgotten in the modern world – is that the
key tool for addressing this kind of problem is conversation.
This distinction is highly significant for the world of business and management, because
most of the important problems that people face in this environment fall into the second
category, the realm of future possibilities – for example, topics such as strategic planning,
investment decisions, cultural change programs and design of new systems and processes.
Indeed, I would argue that any problem which involves human beings, as opposed to mere
numbers, falls into this second category, because in the human environment, nothing is
fixed – there is always potential to change.
In these circumstances it's a tragic irony that modern western culture generally has invested
so heavily in the scientific method, yet forgotten how to have productive conversations. We
live under the illusion that if we can only get the right numbers we'll be able to make a good
decision, when in reality, what we need is a good conversation. For all our emphasis on
technology, we have lost the one technology – conversation – that could make a huge
difference to the success or failure of the futures that we create for ourselves.
The art of strategic conversation
So how do you have a good conversation? Conversations by their very nature are fluid
and flexible, an art rather than a science. Yet there are definitely some natural rhythms and
structures to a good conversation, and a set of simple tools that can be learned to make
conversations far more productive than they often are.
The consulting firm which I work with, 2nd Road1
, has pioneered an approach for
conducting effective conversations as part of our overall goal of creating thinking
1 The name 2nd
Road refers to the fact that the Greeks bequeathed us two roads to truth, the path of rational
scientific analysis based on numbers, and the path of rhetorical argument based on conversation. As
consultants, we have chosen to invest our intellectual capability in developing the second of these roads, the
one that has been neglected for the last 350 years or so of Western culture.

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organisations. Our “Strategic Conversation System™ provides a simple but powerful
generic structure that can be used across a wide range of group planning activities and
problem-solving exercises.2
Strategic conversations have been used with great success in
both the public and private sphere, in large corporations and in small NFP organisations,
across many and varied industries and over very different scales of problem.
Key idea 1: The Thinking Wave™
The first key idea that underpins our process is the idea of the “Thinking Wave™” (see
fig.1). Creative thinking has a rhythm to it, and understanding this rhythm is very helpful for
guiding a conversation to a fruitful outcome. Importantly, there are two quite different sets
of conceptual skills required, depending on how far a group has progressed towards solving
a problem.
In the early stages of the thinking process, we are confronted with a confusing array of
issues, questions, challenges and opportunities. The organisational context is often
complex, and the problem itself can have many layers. Moreover, different people have
different perceptions of where the issues lie. In this “upstream” environment, the sort of
conceptual skills required are fundamentally non-linear and intuitive, as we seek to push
and prod our way through the mass of information and insights to find a pathway that will
lead us forward. It can feel like an uphill battle, but it is a necessary part of understanding a
problem. In most cases, scientific analysis will not be very useful here, except perhaps to
provide some data to consider. The real intellectual work involves reflecting on experience,
forming opinions and weighing up different viewpoints, which is far more the realm where
conversation is a powerful tool.
Strategic decision,
hypothesis
Upstream
 Intuitive
 Complex
 Non-linear
 Fluid
Downstream
 Analytical
 Linear
2 The Strategic Conversation System™ was developed by Tony Golsby-Smith, and has been thoroughly
researched and documented in Tony’s doctoral thesis, “Pursuing the Art of Strategic Conversation”.

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 Systematic
 Structured
Fig. 1 The Thinking Wave™
At the peak of the thinking wave, a strategic decision is made or a hypothesis emerges as
the best way to move forward, and the rhythm changes. A clear direction has been
established and momentum starts to build towards action. The decision or hypothesis may
require some further creative thinking to develop it fully, but there is now a sense of purpose
and increasing clarity. By the end of the thinking wave, but only at the end, it is possible to
apply the analytical, linear, systematic type of thinking that we often associate with planning,
as we put in place structures, timeframes and budgets.
Understanding the rhythm of a strategic conversation helps to protect those running the
meeting from falling into two temptations – the first is to get disheartened when things seem
complex and fluid early on, and to fail to push through to a point of clarity and decision-
making; the second is to rush too quickly to making a decision out of the desire to move
directly into action. Since we were writing essays in school, we have been told that it is
important to invest time in thinking upfront to avoid costly mistakes and wasted effort down
the track, but we still succumb to the illusion that quick action is better than purposeful
reflection.

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Key idea 2: The methodology
The second key element in the Strategic Conversation System™ is the methodology.
In order to move across the Thinking Wave™, a group needs to spend time in four key
places of thought, four “conversation spaces”, which we have labelled A, B, C and D for
easy recall:
A: Where are we now?
A conversation needs to begin with a thorough exploration of the area, structure,
system or process under review. This part of the conversation involves reflection on
past experience, discovery of new insights about what is really going on, as well as
identifying specific problems that need to be addressed.
B: Where do we want to be?
Understanding the present helps us recognise the challenges we face, but does not
create momentum for change. This is why the “B” space is so important. The
group needs to shift gear into a different mental space, one of imagination and
aspiration. We cannot generate any enthusiasm for change without a vision of how
the future could be different, or a dream of what we would like to see in place. The
tension between the present (“A”) and the future (“B”) creates the momentum for
change and engages the desires of the individual members of the group.
C: How do we get there?
Knowing where we want to get to is a great step forward, but the conversation will
ultimately remain fruitless unless we conceive some clearly-defined strategies for
how to get there. This involves both invention (conceiving what we could do) and
judgment (working out which options have the highest priority or would create the
most leverage). This stage of decision-making and direction-setting is vital to crest
the wave and build the downstream momentum.
D: What steps do we need to take?
Only at the end of the process do we start working on an action plan, by defining
what needs to happen next to put our strategies in place, what the timeframes
should be, who we will need to engage and what resources we will need.

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If the Thinking Wave™ gives the person leading the conversation a sense of its flow, then
the methodology provides a clear structure and direction, not only for the leader, but
for the whole group. The approach can be explained in less than five minutes at the
beginning of a conversation, and then serves as a useful reminder to the group about where
the conversation is up to – especially for participants who want to jump straight into
solutions and action before the conceptual thinking has been done.
Key Idea 3: Thinking technologies
A third important component of the whole Strategic Conversation System™ approach is to
recognise that a good conversation needs to be supported by some "thinking technologies",
that is, tools that aid the communication process. Just as scientific analysis is supported
by a set of appropriate techniques and tools, so too the right techniques and tools can make
a big difference to the outcomes of a conversation.
We always recommend that a Strategic Conversation should be led by an external or
internal facilitator, who is well-versed in the methodology and can guide the group through
the process. This frees up the person who is sponsoring the conversation to think about
the content of the discussion, rather than worrying about the process, and also places them
on a more equal footing with the rest of the participants.
A second vital element is an electronic whiteboard. Too many great ideas and important
insights are lost in the midst of a robust conversation, because minimal notes are kept of
the conversation itself – since people believe that only the conclusions or follow-up actions
are important. To overcome this tendency, we map the whole conversation on an electronic
whiteboard, which has several important benefits – it provides a running record of the
conversation, it enables participants to keep track of ideas and make connections between
them, and it also gives scope for a skilled facilitator to create visual models of new ideas
that may be emerging.
Following on from the conversation, we employ two communication technologies to
document the conversation as a whole and the strategic plans that were made. The
TalkBook™ is a blow-by-blow account of the conversation as it unfolded, with all the

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whiteboard printouts collated in a document, and with commentary on facing pages to
capture and synthesise the main ideas. The BlueSheet™ is a one page strategic roadmap,
summarising the main themes of the conversation – the issues that were identified, goals
that were established and strategies put in place – based on the structure.
The joy of strategic conversations
Those who experience a Strategic Conversation for the first time are often surprised and
impressed by the richness of the discussion and the quality of the outcomes. There are a
number of significant benefits to the Strategic Conversation approach:
1. It provides a clear structure to a conversation, giving people a reassuring sense of
direction even when they are grappling with a complex problem, and helping to keep
the train of thinking on track.
2. It engages a number of different thinking skills, including intuition and imagination as
well as reflection and synthesis, which draws out the different conceptual capacities
of those involved.
3. It is a very inclusive and participatory process, so that each person in the group can
contribute on a relatively equal footing and develop a sense of shared discovery and
learning.
4. It creates a powerful sense of common ownership of the problem and shared
purpose towards implementing a solution, which then generates impetus and energy
for following through on the decisions made.
5. It enables management and project teams to think together, rather than working in
silos; to communicate, rather than compete; and to be creative, rather than being
frustrated.
At the end of a Strategic Conversation™, people usually feel relieved that their issues have
been heard, encouraged by the ideas that have emerged, inspired by the prospects for
change and energised to move forward to achieve it. They have discovered that there is
real wisdom that can be drawn from their collective experiences and insights, provided the
right tools are used to unlock it. And for those who have previously been disillusioned by

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meaningless "talkfests" or subjected to the torture of "death by PowerPoint", it is truly a
breath of fresh air.
Julian Jenkins 2005
The Thinking Wave™, methodology, Strategic Conversation™, Talkbook™ and Bluesheet™
are all trademarks of Walsof Pty Ltd.
---------------------------------------------
2nd Road offers both public and internal training courses to teach people the skills of
facilitating a Strategic Conversation™. For more information about the M2M™ (Meeting to
Making™) course and any other 2nd Road products and services, phone the Second Road
office on (02) 9016-1400. 2nd Road can also provide trained facilitators to conduct
Strategic Conversations around a specific project or design issue, or to generate a broad-
ranging strategy across the whole of an organisation.
Julian Jenkins is an experienced workshop facilitator and skilled information designer who
loves to take complex information and communicate it in an accessible and compelling
manner. He works in association with 2nd Road on a wide range of projects combining his
facilitation, writing and design skills to create engaging group conversations, user-friendly
business documents and highly accessible information systems. Based in Sydney, he has
earned high praise for his work with a number of public and private sector clients, which
include PwC, Leighton Holdings, Thiess, the Australian Tax Office and the Defence
Community Organisation. He can be contacted on 0425 240 326 or at
julian@secondroad.com.au.